CA2940269C - Mitochondrial aldehyde dehydrogenase 2 (aldh2) binding polycyclic amides and their use for the treatment of cancer - Google Patents
Mitochondrial aldehyde dehydrogenase 2 (aldh2) binding polycyclic amides and their use for the treatment of cancer Download PDFInfo
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- CA2940269C CA2940269C CA2940269A CA2940269A CA2940269C CA 2940269 C CA2940269 C CA 2940269C CA 2940269 A CA2940269 A CA 2940269A CA 2940269 A CA2940269 A CA 2940269A CA 2940269 C CA2940269 C CA 2940269C
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- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/81—Amides; Imides
- C07D213/82—Amides; Imides in position 3
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- C—CHEMISTRY; METALLURGY
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- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/89—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members with hetero atoms directly attached to the ring nitrogen atom
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- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
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- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/64—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms, e.g. histidine
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- C07D261/02—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings
- C07D261/06—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members
- C07D261/08—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
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- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/22—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D277/30—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
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- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
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- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
- C07D333/24—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
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- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
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- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
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EP3490613A4 (en) * | 2016-07-26 | 2020-03-04 | Cornell University | GENE THERAPY FOR THE TREATMENT OF ALDEHYDE DEHYDROGENASE DEFICIT |
WO2018204673A1 (en) * | 2017-05-05 | 2018-11-08 | The Board Of Trustees Of The Leland Stanford Junior University | Methods and compositions for treating endometriosis and endometriosis associated symptoms |
CN108929263B (zh) * | 2017-05-26 | 2022-07-22 | 中国医学科学院药物研究所 | 芳酰胺类Kv2.1抑制剂及其制备方法、药物组合物和用途 |
WO2019055169A1 (en) * | 2017-09-15 | 2019-03-21 | The Board Of Trustees Of The Leland Stanford Junior University | MITOCHONDRIAL ALDEHYDE DEHYDROGENASE 2 MODULATORS FOR THE PROTECTION, EXPANSION AND INCREASE IN THE POWER OF HEMATOPOIETIC STEM CELLS |
WO2019079209A1 (en) * | 2017-10-16 | 2019-04-25 | Amygdala Neurosciences, Inc. | POLYTHERAPY FOR THE PREVENTION OF AN ADDICTION |
CN108376559B (zh) * | 2018-02-28 | 2020-10-16 | 复旦大学附属中山医院 | 乙醛脱氢酶2基因型在麻醉剂量计算中的应用 |
CN112638881A (zh) * | 2018-07-31 | 2021-04-09 | 普林斯顿大学托管委员会 | 用于治疗转移性和化疗耐受性癌症的四氢喹啉衍生物 |
CA3168533A1 (en) * | 2020-01-24 | 2021-07-29 | The Trustees Of Princeton University | Heterocyclic compounds and uses thereof |
KR102460570B1 (ko) | 2020-02-18 | 2022-10-28 | 주식회사 피코엔텍 | 신규한 돌연변이 효모를 함유하는 아토피 억제 조성물 |
AR123971A1 (es) * | 2020-11-02 | 2023-02-01 | Alchemedicine Inc | Compuesto, agente de activación de aldehído deshidrogenasa 2, composición farmacéutica y fármaco terapéutico y/o profiláctico |
WO2022226383A1 (en) | 2021-04-22 | 2022-10-27 | Kayothera Inc. | Heterocyclic compounds and uses thereof |
WO2023146274A1 (ko) | 2022-01-26 | 2023-08-03 | 서울대학교병원 | 알데히드 탈수소효소 2 조절을 통한 탈모 또는 백모의 예방, 개선, 또는 치료용 조성물 |
CN118591526A (zh) * | 2022-04-22 | 2024-09-03 | 亚克医药株式会社 | 化合物、乙醛脱氢酶2激活剂、药物组合物以及治疗及/或预防药 |
WO2023244574A1 (en) | 2022-06-14 | 2023-12-21 | Amygdala Neurosciences, Inc. | Aldh-2 inhibitor compounds and methods of use |
Family Cites Families (35)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
TW197439B (ko) | 1991-04-04 | 1993-01-01 | Ueno Pharmaceutics Applic Res Co Ltd | |
US5283253A (en) | 1991-09-23 | 1994-02-01 | Florida State University | Furyl or thienyl carbonyl substituted taxanes and pharmaceutical compositions containing them |
WO1993010076A1 (en) | 1991-11-22 | 1993-05-27 | The University Of Mississippi | Synthesis and optical resolution of the taxol side chain and related compounds |
US5200534A (en) | 1992-03-13 | 1993-04-06 | University Of Florida | Process for the preparation of taxol and 10-deacetyltaxol |
JPH08500973A (ja) | 1992-05-21 | 1996-02-06 | ザ ペン ステイト リサーチ ファウンデーション | タキソール、関連タキサン及び他の新規な抗癌/抗ウイルス性化合物原料としてのイチイ培養組織 |
US5274137A (en) | 1992-06-23 | 1993-12-28 | Nicolaou K C | Intermediates for preparation of taxols |
US5294637A (en) | 1992-07-01 | 1994-03-15 | Bristol-Myers Squibb Company | Fluoro taxols |
US5202448A (en) | 1992-08-14 | 1993-04-13 | Napro Biotherapeutics, Inc. | Processes of converting taxanes into baccatin III |
CA2100808A1 (en) | 1992-10-01 | 1994-04-02 | Vittorio Farina | Deoxy paclitaxels |
FR2696461B1 (fr) | 1992-10-05 | 1994-11-10 | Rhone Poulenc Rorer Sa | Nouveaux dérivés d'analogues du taxol, leur préparation et les compositions qui les contiennent. |
FR2696458B1 (fr) | 1992-10-05 | 1994-11-10 | Rhone Poulenc Rorer Sa | Procédé de préparation de dérivés du taxane. |
FR2696463B1 (fr) | 1992-10-05 | 1994-11-25 | Rhone Poulenc Rorer Sa | Procédé d'obtention de la désacétyl-10 baccatine III. |
FR2696464B1 (fr) | 1992-10-05 | 1994-11-10 | Rhone Poulenc Rorer Sa | Nouveau procédé d'estérification de la baccatine III et de la désacétyl-10 baccatine III. |
FR2696462B1 (fr) | 1992-10-05 | 1994-11-25 | Rhone Poulenc Rorer Sa | Procédé d'obtention de la désacétyl-10 baccatine III. |
US5279949A (en) | 1992-12-07 | 1994-01-18 | Board Of Trustees Operating Michigan State University | Process for the isolation and purification of taxol and taxanes from Taxus spp |
US5824701A (en) | 1993-10-20 | 1998-10-20 | Enzon, Inc. | Taxane-based prodrugs |
US5415869A (en) | 1993-11-12 | 1995-05-16 | The Research Foundation Of State University Of New York | Taxol formulation |
WO1998008833A1 (en) | 1996-08-26 | 1998-03-05 | Bristol-Myers Squibb Company | Sulfenamide taxane derivatives |
AU739028B2 (en) | 1996-09-27 | 2001-10-04 | Bristol-Myers Squibb Company | Hydrolyzable prodrugs for delivery of anticancer drugs to metastatic cells |
WO1998022451A1 (fr) | 1996-11-19 | 1998-05-28 | Daiichi Pharmaceutical Co., Ltd. | Derives taxol |
US5977386A (en) | 1996-12-24 | 1999-11-02 | Bristol-Myers Squibb Company | 6-thio-substituted paclitaxels |
WO1998058927A1 (en) | 1997-06-20 | 1998-12-30 | Baker Norton Pharmaceuticals, Inc. | Soluble prodrugs of paclitaxel |
US7288665B1 (en) | 1997-08-18 | 2007-10-30 | Florida State University | Process for selective derivatization of taxanes |
JPH1192468A (ja) | 1997-09-17 | 1999-04-06 | Yakult Honsha Co Ltd | 新規なタキサン誘導体 |
WO1999018113A1 (fr) | 1997-10-08 | 1999-04-15 | Bio Research Corporation Of Yokohama | Derives taxoides et leur procede de production |
FR2847253B1 (fr) * | 2002-11-19 | 2007-05-18 | Aventis Pharma Sa | Nouveaux derives de pyridazinones a titre de medicaments et compositions pharmaceutiques les renfermant |
CA2548254A1 (en) | 2003-12-09 | 2005-06-23 | The Board Of Trustees Of The Leland Stanford Junior University | Methods and compositions for modulating mitochondrial aldehyde dehydrogenase-2 |
CN101111479A (zh) * | 2004-12-16 | 2008-01-23 | 沃泰克斯药物股份有限公司 | 可用作激酶抑制剂的吡啶酮 |
RU2423351C2 (ru) * | 2004-12-16 | 2011-07-10 | Вертекс Фармасьютикалз Инкорпорейтед | Пирид-2-оны, применимые как ингибиторы протеинкиназ семейства тес для лечения воспалительных, пролиферативных и иммунологически-опосредованных заболеваний |
KR20090117950A (ko) * | 2007-03-08 | 2009-11-16 | 더 보드 오브 트러스티스 오브 더 리랜드 스탠포드 쥬니어 유니버시티 | 미토콘드리아 알데히드 탈수소효소-2 조절자 및 그것의 사용 방법 |
KR20110082180A (ko) * | 2008-10-28 | 2011-07-18 | 더 보드 오브 트러스티스 오브 더 리랜드 스탠포드 쥬니어 유니버시티 | 알데히드 탈수소효소의 조절자 및 그것의 사용방법 |
CN102600182B (zh) * | 2012-03-05 | 2013-09-11 | 浙江工业大学 | 苯乙酰氟苯水杨酰胺类化合物在制备抗肺癌药物中的应用 |
CN102614198B (zh) * | 2012-03-05 | 2014-05-14 | 浙江工业大学 | (4-取代苯甲酰)氟苯水杨酰胺类化合物在制备抗肺癌药物中的应用 |
US9670162B2 (en) * | 2013-03-14 | 2017-06-06 | The Board Of Trustees Of The Leland Stanford Junio | Mitochondrial aldehyde dehyrogenase-2 modulators and methods of use thereof |
CN103880700B (zh) * | 2014-03-14 | 2016-05-18 | 浙江工业大学 | O-肉桂酰-氟苯水杨酰胺类化合物及其在制备抗宫颈癌药物中的应用 |
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- 2015-02-19 JP JP2016553529A patent/JP6615769B2/ja active Active
- 2015-02-19 US US15/120,476 patent/US9879036B2/en active Active
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JP2017507147A (ja) | 2017-03-16 |
WO2015127137A1 (en) | 2015-08-27 |
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CN106458910B (zh) | 2020-11-06 |
HUE051255T2 (hu) | 2021-03-01 |
DK3107899T3 (da) | 2020-11-16 |
KR20180135129A (ko) | 2018-12-20 |
JP6615769B2 (ja) | 2019-12-04 |
EP3107899B1 (en) | 2020-08-12 |
KR102319882B1 (ko) | 2021-11-03 |
US20170057982A1 (en) | 2017-03-02 |
PL3107899T3 (pl) | 2021-01-25 |
US9879036B2 (en) | 2018-01-30 |
PT3107899T (pt) | 2020-11-16 |
CA2940269A1 (en) | 2015-08-27 |
CN106458910A (zh) | 2017-02-22 |
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